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Addition of a Cyclophosphine to Nitriles: An Inorganic Click Reaction Featuring Protio, Organo, and Main‐Group Catalysis
Author(s) -
Chitnis Saurabh S.,
Sparkes Hazel A.,
Annibale Vincent T.,
Pridmore Natalie E.,
Oliver Alex M.,
Manners Ian
Publication year - 2017
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201704991
Subject(s) - heterolysis , cycloaddition , chemistry , lone pair , catalysis , yield (engineering) , combinatorial chemistry , organic chemistry , molecule , materials science , metallurgy
The addition of a cyclotriphosphine to a broad range of nitriles gives access to the first examples of free 1‐aza‐2,3,4‐triphospholenes in a rapid, ambient temperature, one‐pot, high‐yield protocol. The reaction produces electron‐rich heterocycles (four lone pairs) and features homoatomic σ‐bond heterolysis, thereby combining the key features of the 1,3‐dipolar cycloaddition chemistry of azides and cyclopropanes. Also reported is the first catalytic addition of P−P bonds to the C≡N bond. The coordination chemistry of the new heterocycles is explored.